2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol | 600168-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol
• 英文别名: (4S,5R)-4-[(1S)-1-azido-2-trityloxyethyl]-2,2-dimethyl-5-tetradecyl-1,3-dioxolane
• CAS: 600168-67-0
• 化学式: C₄₀H₅₅N₃O₃
• 分子量: 625.895
• InChiKey: YVBIDPMQOUIOGR-VYSOZWTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  46
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol 在 三苯基膦 作用下， 以 甲醇 、 溶剂黄146 、 吡啶 、 水 为溶剂， 以65%的产率得到糖脂
  参考文献：
  名称：

  A concise route to phytosphingosine from lyxose

  摘要：

  Phytosphingosine was synthesized from the commercially available D-2,3-O-isopropylidene-D-lyxofuranose in 28% overall yield by a six-step procedure. This procedure is expedient and flexible for introduction of other lipid moieties on the phytosphingosine structure to make a variety of derivatives that can support the further exploration of their related biological functions. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01281-4
• 作为产物：
  描述：

  D-lyxose 在 palladium dihydroxide 三氟甲磺酸酐 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 生成 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol
  参考文献：
  名称：

  A concise route to phytosphingosine from lyxose

  摘要：

  Phytosphingosine was synthesized from the commercially available D-2,3-O-isopropylidene-D-lyxofuranose in 28% overall yield by a six-step procedure. This procedure is expedient and flexible for introduction of other lipid moieties on the phytosphingosine structure to make a variety of derivatives that can support the further exploration of their related biological functions. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01281-4

文献信息

• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
  申请人：Academia Sinica

  公开号：US20160102116A1

  公开（公告）日：2016-04-14

  Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。
• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
  申请人：Academia Sinica

  公开号：US20150071960A1

  公开（公告）日：2015-03-12

  Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and expansion and/or activation of immune cells than those with α-galactose (α-Gal) are disclosed. GSLs bearing α-glucose (α-Glc) and derivatives of α-Glc with F at the 4 and/or 6 positions are provided. Methods for iNKT-independent induction of chemokines by the GSL with α-Glc and derivatives thereof are disclosed. Methods for immune stimulation in humans using GSLs with α-Glc and derivatives thereof are provided.

  提供了带有α-葡萄糖（α-Glc）的糖脂类物质（GSLs），这些物质优先刺激人类不变NKT（iNKT）细胞。公开了具有α-葡萄糖（α-Glc）的GSLs在人类（但在小鼠中较弱）中诱导细胞因子和趋化因子以及扩张和/或激活免疫细胞的能力强于具有α-半乳糖（α-Gal）的物质。提供了带有α-葡萄糖（α-Glc）和α-Glc在4和/或6位置带有F衍生物的GSLs。公开了使用带有α-Glc及其衍生物的GSL对趋化因子进行iNKT独立诱导的方法。提供了使用带有α-Glc及其衍生物的GSL在人类中进行免疫刺激的方法。
• An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells
  作者：Janice M.H. Cheng、Stephanie H. Chee、Deborah A. Knight、Hans Acha-Orbea、Ian F. Hermans、Mattie S.M. Timmer、Bridget L. Stocker

  DOI：10.1016/j.carres.2011.02.014

  日期：2011.5

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes
  作者：Gang-Ting Fan、Yi-shin Pan、Kuo-Cheng Lu、Yu-Pei Cheng、Wan-Chen Lin、Steven Lin、Chun-Hung Lin、Chi-Huey Wong、Jim-Min Fang、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.12.027

  日期：2005.2

  Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive D-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6OH underwent glycosylation in excellent alpha-anomeric selectivity. A variety of alpha-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids were prepared, and their activities involved in the proliferation of mouse splenocytes and the expression of cytokines were elucidated. Besides alpha-galactosyl ceramides, a galactosyl serine-type lipid also exhibited substantial effect on the expression of cytokines IFN-gamma and IL-4. (C) 2004 Elsevier Ltd. All rights reserved.
• A concise route to phytosphingosine from lyxose
  作者：Chun-Cheng Lin、Gang-Ting Fan、Jim-Min Fang

  DOI：10.1016/s0040-4039(03)01281-4

  日期：2003.7

  Phytosphingosine was synthesized from the commercially available D-2,3-O-isopropylidene-D-lyxofuranose in 28% overall yield by a six-step procedure. This procedure is expedient and flexible for introduction of other lipid moieties on the phytosphingosine structure to make a variety of derivatives that can support the further exploration of their related biological functions. (C) 2003 Published by Elsevier Science Ltd.